Dailey Resources

Do you hold Offsite Retreats for Your Business?

May 29, 20251 min read

This past week, I had the privilege of spending a few days at an offsite conference with Katrina and Heather, two exceptional leaders within our organization. The experience underscored the significant benefits of taking your team "offsite" to cultivate clarity, foster connections, and enhance culture.

Key Realizations from Our Retreat:

  • The Necessity of Scheduling Time: Allocating time for offsite engagements with leaders is essential. Though it may seem difficult to justify the financial cost and the time away from other activities, with the right people, this is not merely an expense—it's an investment in our future.

  • Gaining New Perspectives: Being offsite allows us to view our daily challenges from a fresh perspective. It's about rising above the immediate obstacles to see the broader picture—or as we say, floating above the trees to see the forest.

  • Valuing Connection: Some of the most important work happens when we connect on a human level. Sharing meals and experiences allows us to engage beyond work topics. These interactions are invaluable, and frankly, these are moments I would not prioritize as much without deliberately scheduling them.

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Reflective Questions to Consider:

  1. How frequently do you set aside time to retreat with your team or leadership?

  2. Do you view these retreats as a mere expense or as a vital investment?

  3. Are you consistently investing in both the personal and professional growth of your team members?

  4. Consider a team member’s inclusion in training or offsite activities. If you hesitate, asking "Are they worth it?" what does that indicate? It might suggest a view of these activities as expenses rather than investments. Alternatively, it might reveal doubts about their fit within your core team. If you're reluctant to invest in someone's participation, perhaps they shouldn't be on your team—a thought worth pondering.

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Seth is the Co-Founder of both The Dailey Group and Keller Williams Gateway in Baltimore, Maryland. He serves as the Operating Principal for the brokerage and as the team leader for The Dailey Group, which consistently helps over 150 families a year. Seth, a Montana native, is passionate about empowering leaders and teaching people to make smart financial moves.

Prior to real estate, Seth held his CPA designation and worked as a mortgage lender before joining forces with his wife of 20 years, Alyce. Seth can usually be found at the nearest coffee shop with a personal growth book in hand while scribbling down his next great idea on the back of a napkin.

Seth Dailey

Seth is the Co-Founder of both The Dailey Group and Keller Williams Gateway in Baltimore, Maryland. He serves as the Operating Principal for the brokerage and as the team leader for The Dailey Group, which consistently helps over 150 families a year. Seth, a Montana native, is passionate about empowering leaders and teaching people to make smart financial moves. Prior to real estate, Seth held his CPA designation and worked as a mortgage lender before joining forces with his wife of 20 years, Alyce. Seth can usually be found at the nearest coffee shop with a personal growth book in hand while scribbling down his next great idea on the back of a napkin.

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